Hydrazine hydrate (1:1) → HCID 22506179, compound

HRID 1814426Notes

Reaction equation

HRID 1814426 reaction equation
[OH:1][CH:2]([CH2:21][N:22]1[C:26](=[O:27])C2=CC=CC=C2C1=O)[CH2:3][N:4]([CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)[CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].O.NN.[Br:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]=C=O)=[CH:39][CH:38]=1.CO.C(Cl)(Cl)Cl>CCO>[Br:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:26](=[O:27])[NH:22][CH2:21][CH:2]([OH:1])[CH2:3][N:4]([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)[CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 756094-Bromophenyl isocyanateHCID 20771341HCID 20771341, compoundHCID 21584188Chloroform methanol

Product 1

HCID 22506179HCID 22506179, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4[[2-hydroxy-(3-phthalimido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butanoic acid (68 mg, 0.16 mmol) in EtOH (1 ml) was added hydrazine monohydrate (38 μl, 0.78 mmol), and the mixture was stirred at RT for 3 h. The reaction mixture was concentrated under vacuum to dryness, and the residue was suspended in CH2Cl2 (2 ml). To the suspension was added 4-bromophenyl isocyanate (47 mg, 0.24 mmol), and the mixture was stirred at RT for 40 h. The reaction mixture was adsorbed on a plate of silica gel and then developed with 10% methanol/chloroform to afford 4-[[3-(4-bromophenylureido)2-hydroxypropyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butanoic acid (13 mg, 16%): MS(ES+) m/e 504 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.74 (s, 1H), 8.07 (br, 2H), 7.62 (d, J=7.6 Hz, 1H), 7.36 (m, 4H), 7.13-7.00 (m, 3H), 6.15 (m, 1H), 3.92 (m, 1H), 3.66-3.45 (m, 3H), 2.70 (m, 1H), 2.67 (m, 2H), 2.51 (m, 2H), 2.36 (m, 2H), 2.25 (m, 1H), 2.14 (m, 1H), 2.02 (m, 1H), 1.19 (m, 1H), 1.67-1.49 (m, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum to dryness
  2. stirringthe mixture was stirred at RT for 40 h

Sources & evidence

ORD record
ord-300abf02e92340059a0c2fd004c569f1
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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